Middleburg Virginia Entertainment & Events

Antique Shows & Auctions

Hunt Country Winter Antiques Show
Located at The Hill Middle School
434-823-5329
An annual show held in January with over 50-dealers and hundreds of visitors. The show features antique furniture, paintings, silver, vintage fashions, books, pottery, porcelain & china, and more. more...

Christmas in Middleburg
Town of Middleburg
540-687-8888
Enjoy this holiday celebration in the quaint capital of horse country that includes two parades, breakfast with Santa, live music, arts & crafts, food and more. The local hunt club parades down Washington Street, creating a spectacular scene of hounds followed closely by nearly 100 horses and riders in red riding coats. Later, an old-fashioned Christmas parade ends with the arrival of Santa Claus. more...
Norton Wine and Bluegrass Festival
23876 Champe Ford Road • Middleburg, VA 20117
Chrysalis Vineyards
540-687-8222
Visit Chrysalis Vineyards in the midst of harvest and experience the hottest festival of the year. Enjoy bluegrass and many other bands throughout the weekend, craft and food vendors, hay rides, vineyard tours, a special wine tasting with commemorative take home glasses, and more. Sample all of their Norton wines, purchase some of their library vintage Nortons, and refresh from the sun with their Sarah's Patio Red. more...

Virginia Fall Races
Located at Glenwood Park
540-687- 5152
The only two-day steeplechase meet in Virginia, hosting over ten action-packed races, this world-class sporting event is an annual fall tradition which takes place in October and offers visitors a chance to see steeplechase action at the oldest continuous race course in the state of Virginia. more...

Hunt Country Stable Tour
Located In and Around Upperville
540-592-3711
The Upperville area is home to many of the country's premier thoroughbred breeding farms, show hunter barns, and country estates and each year on Memorial Day weekend, owners of these properties welcome visitors and open the gates of their exquisite grounds, magnificent stables, and extensive training facilities. more...